Qiang Wang, Wei-Zhen Wang, Ruiying Zhang, Zi'ang Zhai, Xinyu Chen, Minggang Li, Yi Jin, Lingyun Zhu, Yuanming Li, Ke-Yin Ye
{"title":"Benzo-Extended [<i>n</i>]Phenacenes: e‑Flow Synthesis and Length-Dependent Properties.","authors":"Qiang Wang, Wei-Zhen Wang, Ruiying Zhang, Zi'ang Zhai, Xinyu Chen, Minggang Li, Yi Jin, Lingyun Zhu, Yuanming Li, Ke-Yin Ye","doi":"10.1021/jacsau.5c00653","DOIUrl":null,"url":null,"abstract":"<p><p>This study presents an efficient method for synthesizing twisted benzo-extended [<i>n</i>]-phenacenes ([<i>n</i>]-BPs) featuring an electrochemical flow (e-flow) Scholl reaction of the corresponding [<i>n</i>]-BP precursors from a one-pot three-component Suzuki-Miyaura coupling reaction. The e-flow Scholl reaction offers advantages such as reduced oxidant usage and overoxidation byproducts, and easy scale-up through extended electrolysis time toward these intricate polycyclic aromatic hydrocarbons. In addition, the increase in molecular length decreases the optical bandgap of [<i>n</i>]-BPs and thus tunes their photophysical properties. This work provides a green and sustainable synthetic strategy for diverse [<i>n</i>]-BPs and enables facile bandgap modulation through π-conjugation extension, offering potential for organic semiconductor applications in optoelectronic devices.</p>","PeriodicalId":94060,"journal":{"name":"JACS Au","volume":"5 9","pages":"4281-4287"},"PeriodicalIF":8.7000,"publicationDate":"2025-09-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC12458015/pdf/","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"JACS Au","FirstCategoryId":"1085","ListUrlMain":"https://doi.org/10.1021/jacsau.5c00653","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"2025/9/22 0:00:00","PubModel":"eCollection","JCR":"Q1","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
引用次数: 0
Abstract
This study presents an efficient method for synthesizing twisted benzo-extended [n]-phenacenes ([n]-BPs) featuring an electrochemical flow (e-flow) Scholl reaction of the corresponding [n]-BP precursors from a one-pot three-component Suzuki-Miyaura coupling reaction. The e-flow Scholl reaction offers advantages such as reduced oxidant usage and overoxidation byproducts, and easy scale-up through extended electrolysis time toward these intricate polycyclic aromatic hydrocarbons. In addition, the increase in molecular length decreases the optical bandgap of [n]-BPs and thus tunes their photophysical properties. This work provides a green and sustainable synthetic strategy for diverse [n]-BPs and enables facile bandgap modulation through π-conjugation extension, offering potential for organic semiconductor applications in optoelectronic devices.
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